The Claremont Indecent: The roommate, the Wordsworth routine, and the one-night stand

Multi-colored candy hearts are laid out on a table.
Sleepless on Sixth Street reminisces on the highs and lows of three hookups from their freshman year. (Courtesy: Pixabay)

Hey Claremont… you up? I heard you asking for it — nay, begging for it — so TSL’s sex column is back, and it’s going to be a spiiiiccccy semester. But why me, you may be asking? Well, let me tell you some tales of hookups past. 

Freshman year was a whirlwind for me, as it was for so many of us. I never had a stable hookup in high school, let alone a steady relationship. College was like being a kid in a candy shop, and boy, was I in for a sugar high. 

My first target was a boy who lived just three doors down. It’s week one, and let me just say: I’m not proud of this one. But convenient is convenient, and I was ready to dip my toes in the water of this new college-size dating pool. So how very fortunate it was that the boy — we’ll call him #1 — wanted to watch “Mamma Mia!” in my room with a few other hallmates. Even more fortuitous, the other hallmates left promptly after Donna said “I do.” 

There was just one small inconvenience: my roommate, asleep on her side of the room. The makeout session that ensued was simply not in good taste, I’ll admit it. But #1 and I were a dedicated bunch — until we were rudely interrupted by none other than my roommate. Some loud exclamations in sleeptalk were convincing enough to give me and my makeout buddy quite a fright. Ashamedly, we resorted to the laundry room.

So maybe that choice was a little too close to home. Having learned that lesson, I decided to branch out a bit. And I got as far as… my first year writing seminar. 

I was lured in by the dark, shaggy hair, what can I say? So when I came across boy #2 in my dorm hallway one Saturday night, of course I offered to braid it. Soon braiding turned into kissing, and kissing turned into a story I would recount to my friends in the morning as the most romantic evening of my entire life. 

I’ll recount it to you, too: he did card tricks for me. He serenaded me with guitar. He whipped out a book of Wordsworth poetry to read to me, then recited from memory the last page of “The Great Gatsby.” We cuddled in a hammock and talked sentimentally about our families, and then he bought me a grilled cheese. I was euphoric. 

The next day at dinner, I was still talking about my night with #2. This time, though, a friend of a friend overheard my detailed sequence of events. “Oh, did you get with #2?” she inquired. A bit surprised, I confirmed that he was the guy. 

As it turns out, she had done the same. Moreover, he had done the same. 

After some quality comparing and contrasting, we discovered he had used all the same moves on her: the guitar, the Wordsworth, the hammock heart-to-heart. Everything, every detail was the same — down to the grilled cheese. Even better, he watched these discoveries unfold from just a few tables away.

Last — but certainly not least — let me tell you about my “first time” (and preface it by saying: virginity is a social construct, designed to intimidate, proselytize and promote heteronormativity… But we knew that already). So on with how I “lost” mine. 

The night began with a text from #2, in fact, asking me to come to his room for a chat. Teeming with curiosity, I made my way over, only to be met with the “I really don’t want anything serious” talk. I’m sure you’re as shocked as I was. Well, after the dinner debacle, I agreed to his terms and we hooked up for a bit, but never mind that. The night still young, we then made our way to a glorious dorm basement party lit entirely by flashing LED disco balls. Not 30 seconds in, we ran into a boy from my hall — no, not #1… a different one. (Perhaps I hadn’t learned my lesson after all.)

With some sort of strobe-induced, spite-driven determination, I went ahead and upgraded from #2 for #3. We promptly left for his room in lieu of the party and started hooking up. Soon enough, we reached the inevitable, awkward point of the “Do you want to?” conversation. I said yes, but that I hadn’t before, and he said he hadn’t either, which made me feel better. It was a pretty unsuccessful attempt, and involved a lot of fumbling and readjusting. In one word, the sex was underwhelming. Unfortunately, it took a turn for the worse. In our post-coital cuddles, the first thing he said was, “So… this was a one night stand.”

So maybe, after these three less-than-ideal incidents, you’re thinking, “How is Sleepless qualified to give advice?” But to that I say: maybe the best advice is that sex is a tricky business, full of trial and error, missed marks and mishaps. I’m here to be your reassurance that things go wrong and to be the confidence boost you need to make things go right. So let’s make this semester a steamy one, Claremont. I know I’m just getting started.

Much love, 

Sleepless on Sixth Street 

P.S. Have questions, thoughts or concerns of your own? This completely anonymous Google Form is just for you: Share away!

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